Trifluoroacetic acid → HCID 54455838, compound

HRID 868338Notes

Reaction equation

HRID 868338 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[CH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][N:33]([CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:32][CH2:31]2)=[O:24])=[N:19][CH:20]=1)=[O:14])(C)(C)C>ClCCl>[C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[CH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][N:33]([CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:34][CH2:35]2)=[O:24])=[N:19][CH:20]=1)([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54434533HCID 54434533, compound

Product 1

HCID 54455838HCID 54455838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 ml) is cooled to 5° C., and a solution of 0.8 g of N-[3-(5-t-butoxycarbonyl-2-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine (the free base of the product of Example 24) in 3 ml of dichloromethane is slowly added below 20° C. The mixture is stirred at room temperature overnight and concentrated. The residue is dissolved in 10 ml of water and washed with diethyl ether. The aqueous solution is adjusted to pH 5 with aqueous ammonium hydroxide and extracted with three 40-ml portions of ethyl acetate. The combined extracts are dried over magnesium sulfate and the solvent is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (10:1) to give the title compound. m.p. 214°-216° C. (recrystallized from methanol)

Workup

  1. customis slowly added below 20° C
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in 10 ml of water
  4. washwashed with diethyl ether
  5. extractionextracted with three 40-ml portions of ethyl acetate
  6. dry with materialThe combined extracts are dried over magnesium sulfate
  7. distillationthe solvent is distilled off
  8. customThe residue is chromatographed on silica gel with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-6259a0c20da04f689577e553fbfb9891
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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